ChemFOnt: Showing chemical card for Disialyllacto-N-tetraose (CFc000002835)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:48 UTC

Chemfont ID

CFc000002835

Molecule Identification

Common Name

Disialyllacto-N-tetraose

Definition

Disialyllacto-N-tetraose is a sialyl hexasaccharide from human milk, which has also been isolated from the urine of pregnant women and has also been found in the feces of preterm human newborns. Its structure is that of lacto-N-tetraose with one of the residues of sialic acid linked alpha-(2->3) to the terminal nonreducing residue of D-galactose and the other sialic acid residue linked alpha-(2->6) to the N-acetyl-D-glucosamine residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID:10683228 , 809156 , 5363606 , 1000529 , 3421714 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Di-N-acetylneuraminosyllacto-N-tetraose	HMDB
NeuAc-alpha-(2-3)-gal-beta-(1-3)-neuac-alpha-(2-6)-glcnac-beta-(1-3)-gal-beta-(1-4)-GLC	MeSH, HMDB
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-3-hydroxy-5-[(1-hydroxyethylidene)amino]oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB
Disialyllacto-N-tetraose	MeSH

Chemical Formula

C₄₈H₇₉N₃O₃₇

Average Molecular Weight

1290.1388

Monoisotopic Molecular Weight

1289.439240557

IUPAC Name

(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-3-hydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

CAS Registry Number

61278-38-4

SMILES

[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)[C@@H]2O)[C@H](NC(C)=O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C48H79N3O37/c1-12(57)49-23-15(60)4-47(45(74)75,86-37(23)26(64)17(62)6-52)78-11-22-30(68)36(25(51-14(3)59)42(82-22)85-39-28(66)19(8-54)80-43(33(39)71)83-35-21(10-56)79-41(73)32(70)31(35)69)84-44-34(72)40(29(67)20(9-55)81-44)88-48(46(76)77)5-16(61)24(50-13(2)58)38(87-48)27(65)18(63)7-53/h15-44,52-56,60-73H,4-11H2,1-3H3,(H,49,57)(H,50,58)(H,51,59)(H,74,75)(H,76,77)/t15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25+,26+,27+,28-,29-,30+,31+,32+,33+,34+,35+,36+,37+,38+,39-,40-,41?,42-,43-,44-,47+,48-/m0/s1

InChI Key

FCIROHDMPFOSFG-LAVSNGQLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

Oligosaccharide
N-acylneuraminic acid
Neuraminic acid
N-acyl-alpha-hexosamine
C-glucuronide
Glycosyl compound
C-glycosyl compound
O-glycosyl compound
Ketal
Dicarboxylic acid or derivatives
Pyran
Oxane
Acetamide
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Carbonyl group
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Breast milk (PMID: 10683228)
Breast milk (HMDB: HMDB0006594)

Excreta

Biofluid or Excreta

Feces (PMID: 23210743)

Source

Endogenous

Endogenous (HMDB: HMDB0006594)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	153 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-13	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	37	ChemAxon
Hydrogen Donor Count	24	ChemAxon
Polar Surface Area	647.8 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	264.81 m³·mol⁻¹	ChemAxon
Polarizability	122.48 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0006594

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023991

KNApSAcK ID

Not Available

Chemspider ID

2342164

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3085216

PDB ID

Not Available

ChEBI ID

89907

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Disialyllacto-N-tetraose (CFc000002835)

MOL for CFc000002835 (Disialyllacto-N-tetraose)

3D MOL for CFc000002835 (Disialyllacto-N-tetraose)

3D SDF for CFc000002835 (Disialyllacto-N-tetraose)

3D-SDF for CFc000002835 (Disialyllacto-N-tetraose)

PDB for CFc000002835 (Disialyllacto-N-tetraose)

3D PDB for CFc000002835 (Disialyllacto-N-tetraose)

SMILES for CFc000002835 (Disialyllacto-N-tetraose)

INCHI for CFc000002835 (Disialyllacto-N-tetraose)

Structure for CFc000002835 (Disialyllacto-N-tetraose)

3D Structure for CFc000002835 (Disialyllacto-N-tetraose)